Thionyl Chloride → 4-(chloromethyl)-1-propyl-1H-imidazole

HRID 332150Notes

Reaction equation

HRID 332150 reaction equation
[CH2:1]([N:4]1[CH:8]=[C:7]([CH2:9]O)[N:6]=[CH:5]1)[CH2:2][CH3:3].O=S(Cl)[Cl:13]>C(Cl)Cl>[Cl:13][CH2:9][C:7]1[N:6]=[CH:5][N:4]([CH2:1][CH2:2][CH3:3])[CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 124932744-Hydroxymethyl-1-propylimidazole

Product 1

HCID 229385374-(chloromethyl)-1-propyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-propyl-1H-imidazol-4-yl)methanol (535 mg, 3.11 mmol) was first treated with SOCl2 (3 ml) in CH2Cl2 (5 ml) at 35° C. for 2 hrs. The solvent was removed to get a crude 4-(chloromethyl)-1-propyl-1H-imidazole. Then following General Procedure A, the title compound (587 mg, 67%) was prepared from 2-amino-4-chlorobenzenethiol (744 mg, 4.66 mmol), 4-(chloromethyl)-1-propyl-1H-imidazole, K2CO3 (2.1 g, 15.54 mmol) in DMF (10 ml).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-3a71f63ff61c4d75bb885f6302540c58
Source dataset
uspto-grants-2014_11
Patent number
US08877804B2

Reaction notes

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